It’s August 15, and we’re bored by caftans. But since we’ve got weeks of swimming weather ahead of us, and we aren’t stocking up on fall work clothes this year, we might as well expand our beachwear collection with a kicky playsuit from the new Australian brand Terry. Reminiscent of something that Megan Draper might have worn around a kidney-shaped pool in Los Angeles, this all-in-one outfit feels like a towel but looks perfectly polished on Zoom (from the waist up, anyway). ($255, matchesfashion.com)

The fact of the matter is that some offices are reopening. Despite recent arguments that fashion, in general, may be “over,” those sweatpants you’ve been wearing since March won’t be welcome in your next board meeting. Ease back into a more buttoned-up approach to dressing with a polo and matching midi skirt from Proenza Schouler. Fret not—it has an elastic waist, but the tailored silhouette and beautiful knit communicate gravitas. Baby steps. (skirt, $890; polo; $790; net-a-porter.com)

Over at Issimo, Air Mail editor at large Marie-Louise Sciò is curating some of the best Italian fashion out there. We’re especially charmed by these W.F.H.-friendly Friulian slippers by Oséree. They nod to the traditional Venetian slippers, but the gold Lurex adds a bit of attitude. Matching bathing suit recommended but not required. ($136, issimo.com)

Fall is coming, city life beckons, and we will eventually emerge from confinement. So, yes, it’s time to return to tailoring. In the realm of women’s wear, few designers pay adequate attention to trousers. So when we spot a pair this appealing from Jacquemus—high-waisted, wide-legged, and as trend-proof as we could hope for—we snap them up without second-guessing. It’s true: these would have looked right at home in the 70s, but if all goes according to plan, they’ll look just as stylish 40 years from today. ($505, modaoperandi.com)